Toluene → HCID 21890866, compound

HRID 721881Notes

Reaction equation

HRID 721881 reaction equation
C1(CCC(Cl)=O)CCCC1.[CH:11]1([CH2:16][CH2:17][C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12]1.[Cl:23][C:24]1[CH:30]=[C:29]([O:31][C:32]2[C:41]3[C:36](=[CH:37][C:38]([O:44][CH3:45])=[C:39]([O:42][CH3:43])[CH:40]=3)[N:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][C:25]=1[NH2:26].C1(C)C=CC=CC=1>C(O)C>[CH:11]1([CH2:16][CH2:17][C:18]([N:20]=[C:21]=[S:22])=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15]1.[Cl:23][C:24]1[CH:30]=[C:29]([O:31][C:32]2[C:41]3[C:36](=[CH:37][C:38]([O:44][CH3:45])=[C:39]([O:42][CH3:43])[CH:40]=3)[N:35]=[CH:34][CH:33]=2)[CH:28]=[CH:27][C:25]=1[NH:26][C:21]([NH:20][C:18](=[O:19])[CH2:17][CH2:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)=[S:22]

Participants

7

Reactant 4

HCID 1140TolueneHCID 660393-Cyclopentylpropionyl chlorideHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroanilineHCID 16775438HCID 16775438, compound

Product 2

HCID 16775438HCID 16775438, compoundHCID 21890866HCID 21890866, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Cyclopentylpropanoyl isothiocyanate was prepared using commercially available 3-cyclopentylpropanoyl chloride (80 mg) as a starting compound according to the description of the literature. 3-Cyclopentylpropanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (32 mg, yield 41%).

Workup

  1. customto prepare a solution
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b44ca41416614829a19033950b7f8057
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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